Can Older Women, Younger Men Relationships Work?

There’s no question that thinking about cougar-cub pairings like Demi Moore and Ashton Kutcher —or Jane Seymour chasing Owen Wilson in Wedding Crashers—raises a lot of, well, questions. Why do women, who typically gravitate toward older men, decide they want to date significantly younger men? Why do men, given the science of dating hot younger chicks, decide to chase an older one? And once you’ve taken the plunge, how do you make it work? Having a relationship with a woman your own age is hard enough. While having flings with hot older women can be a blast, research shows that making it last is a whole other matter.

An AARP magazine survey showed 34 percent of women over 40 date younger men. Cougaring is no passing fancy; it’s a phenomenon that’s here to stay. Many older women reported liking younger men for obvious reasons: more energy, more enthusiasm, and best of all less baggage. Whereas a man in his 40s has probably been married (and possibly divorced) at least once, men in their 20s and 30s have a fresher, less jaded perspective on life. But what the hell do younger men want with older women, then?

Well, frankly, cougars tend to have the same mindset as young men. Women in their 40s and 50s are often over the marriage and kids thing. They don’t want someone to provide for their needs—they can do that themselves. Rather than having to navigate a Byzantine maze of emotional needs, with a cougar you can get right down to hanging out, having fun together and, of course, screwing. Your very own Mrs. Robinson might not want you for anything serious, but who cares? As a man, you’re getting what you want—namely, no strings attached sex.

The good: when you’re dating an older woman, she knows what she wants and generally isn’t shy about going after it. While not in the shape she was 10 years ago, no matter how good the personal trainer, she does know her way around the boudoir more than most chicks your age. Further, she likely has a successful career and steady income. A cougar will almost never look to you for support, financial or otherwise.

The bad: The biggest downside to dating an older woman (other than gravity and time) is the aforementioned baggage. While you’re still young and fresh, she’s been around the block. If it isn’t showing physically, it’s can still show emotionally. Particularly after a divorce or two, some cougars can be bitter, jaded and not a lot of fun at all.

Making a cougar relationship work can be hard. Dr. Adam Scheck, an LA-based clinical psychologist and couples counselor, believes that cougar relationships occurring organically have a better chance than ones where a hunting cougar has snared prey, or vice versa. Indeed, whether a cougar is involved or not, relationships built on trophy hunting rarely work out in the long run.

When you’re looking for success with an older woman, you need maturity, sensitivity and charm. While certain problems are specific to a cougar-cub relationship, like different health cycles and potentially awkward social situations, most relationship issues encountered in older woman, younger man relationships are the same as in any other. Find more insights in the stories below. You kids have fun.